Ammonia → HCID 12140598, compound

HRID 2279937Notes

Reaction equation

HRID 2279937 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:17].C[Si]([C:22]#[N:23])(C)C>CO>[NH2:17][CH:12]([C:11]1[CH:14]=[CH:15][CH:16]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)[C:22]#[N:23]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 743423-BenzyloxybenzaldehydeHCID 82115Trimethylsilyl cyanide

Product 1

HCID 12140598HCID 12140598, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-benzyloxybenzaldehyde (2.12 g, 10 mmol) in a 7N ammonia solution in methanol (50 mL) at 0° C. was added trimethylsilyl cyanide (1.11 mL, 15 mmol) dropwise. The resulting mixture was stirred at 0° C. for 10 min, warmed to 45° C. for 18 h and concentrated to dryness. The crude material was purified by silica gel column chromatography, eluting with 0-100% dichloromethane/10% methanol in dichloromethane, to afford the title compound (1.26 g, 53%) as a thick orange oil.

Workup

  1. temperaturewarmed to 45° C. for 18 h
  2. concentrationconcentrated to dryness
  3. customThe crude material was purified by silica gel column chromatography
  4. washeluting with 0-100% dichloromethane/10% methanol in dichloromethane

Sources & evidence

ORD record
ord-e25c56fc238d41babcef65b1b9283c85
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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